2-(trifluoroacetamido)-4-(chloromethyl)thiazole | 152531-39-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(trifluoroacetamido)-4-(chloromethyl)thiazole
• 英文别名: N-[4-(chloromethyl)-1,3-thiazol-2-yl]-2,2,2-trifluoroacetamide
• CAS: 152531-39-0
• 化学式: C₆H₄ClF₃N₂OS
• 分子量: 244.625
• InChiKey: GGZUZCNTWAMPAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  potassium thioacyanate 、 2-(trifluoroacetamido)-4-(chloromethyl)thiazole 在 potassium iodide 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以67%的产率得到2-amino-4-(isothiocyanatomethyl)thiazole
  参考文献：
  名称：

  Synthesis of 2,4-disubstituted thiazoles and selenazoles as potential antifilarial and antitumor agents. 2. 2-Arylamido and 2-alkylamido derivatives of 2-amino-4-(isothiocyanatomethyl)thiazole and 2-amino-4-(isothiocyanatomethyl)selenazole

  摘要：

  The synthesis of a series of 2-arylamido and 2-alkylamido derivatives of 2-amino-4-(isothio-cyanatomethyl)thiazole and 2-amino-4-(isothiocyanatomethyl)selenazo is described. In vitro antiproliferative evaluations were carried out using L1210 cells. The 2-(alkylamido)thiazole derivatives were moderately antiproliferative, with IC50's of 4-8 mu M. A significant increase in activity was obtained for the arylamido derivatives, with IC50's of 0.2-1 mu M. The results obtained for the selenazoles were similar to those for the thiazoles. 2-Benzamido-4-(isothiocyanatomethyl)thiazole (19) was found to be a potent inhibitor of GMP synthetase. None of the compounds prepared in this study demonstrated antifilarial activity.

  DOI：

  10.1021/jm00076a013
• 作为产物：
  描述：

  4-(chloromethyl)thiazol-2-amine hydrochloride 、 三氟乙酸酐 反应 6.0h， 以98%的产率得到2-(trifluoroacetamido)-4-(chloromethyl)thiazole
  参考文献：
  名称：

  Synthesis of 2,4-disubstituted thiazoles and selenazoles as potential antifilarial and antitumor agents. 2. 2-Arylamido and 2-alkylamido derivatives of 2-amino-4-(isothiocyanatomethyl)thiazole and 2-amino-4-(isothiocyanatomethyl)selenazole

  摘要：

  The synthesis of a series of 2-arylamido and 2-alkylamido derivatives of 2-amino-4-(isothio-cyanatomethyl)thiazole and 2-amino-4-(isothiocyanatomethyl)selenazo is described. In vitro antiproliferative evaluations were carried out using L1210 cells. The 2-(alkylamido)thiazole derivatives were moderately antiproliferative, with IC50's of 4-8 mu M. A significant increase in activity was obtained for the arylamido derivatives, with IC50's of 0.2-1 mu M. The results obtained for the selenazoles were similar to those for the thiazoles. 2-Benzamido-4-(isothiocyanatomethyl)thiazole (19) was found to be a potent inhibitor of GMP synthetase. None of the compounds prepared in this study demonstrated antifilarial activity.

  DOI：

  10.1021/jm00076a013

文献信息

• Synthesis of 2,4-disubstituted thiazoles and selenazoles as potential antifilarial and antitumor agents. 2. 2-Arylamido and 2-alkylamido derivatives of 2-amino-4-(isothiocyanatomethyl)thiazole and 2-amino-4-(isothiocyanatomethyl)selenazole
  作者：Yatendra Kumar、Rachel Green、Dean S. Wise、Linda L. Wotring、Leroy B. Townsend

  DOI：10.1021/jm00076a013

  日期：1993.11

  The synthesis of a series of 2-arylamido and 2-alkylamido derivatives of 2-amino-4-(isothio-cyanatomethyl)thiazole and 2-amino-4-(isothiocyanatomethyl)selenazo is described. In vitro antiproliferative evaluations were carried out using L1210 cells. The 2-(alkylamido)thiazole derivatives were moderately antiproliferative, with IC50's of 4-8 mu M. A significant increase in activity was obtained for the arylamido derivatives, with IC50's of 0.2-1 mu M. The results obtained for the selenazoles were similar to those for the thiazoles. 2-Benzamido-4-(isothiocyanatomethyl)thiazole (19) was found to be a potent inhibitor of GMP synthetase. None of the compounds prepared in this study demonstrated antifilarial activity.